I’ve know Judy since high school. We dated briefly, hooked up multiple times in college (different universities a few hours apart)…this is the story of one of the best of those hook ups.
Neither of us were dating anyone and Judy asked if she could come visit for the weekend for some ‘fun’ and to pay up on loosing a bet we had over our schools football game. We won and I told her it was time to pay up. I let my roommates know Judy was coming up. They both knew her from previous visits and road trips. She rolled in late on Friday and we headed to the bar right by our house for some beers and catching up.
One of my roommates, Kevin, was with me when Judy walked in. We were all chit chatting when the subject of the bet came up. Kevin asked what Judy would have to do to ‘pay up’. I said I wasn’t sure yet….so he offered up an idea. He knew she loved wearing skirts even in the winter and she would certainly have some to wear this weekend even though it was winter and only in the 20° at night. His suggestion: Judy would wear her shortest skirt out the next night….without panties, all night as we bar hopped.